Chloroacetyl chloride → 2-Chloroacetamido-5-methoxy phenol

HRID 892351Notes

Reaction equation

HRID 892351 reaction equation
COC1C=CC2N=CCOC=2C=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[OH:22].[Cl:23][CH2:24][C:25](Cl)=[O:26]>CC(C)=O>[Cl:23][CH2:24][C:25]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[OH:22])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 99421632-Amino-5-methoxyphenol2×HCID 541344017-Methoxy-1,4-benzoxazine

Product 1

HCID 135065532-Chloroacetamido-5-methoxy phenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Hill and Ramage reported at J. Chem. Soc., 3709 (1964) a convenient synthesis of 7-methoxy-1,4-benzoxazine from 2-amino-5-methoxyphenol 9a. Compound 9a reacted with chloroacetyl chloride in acetone to give 2-chloroacetamido-5-methoxy phenol 10a. An intramolecular cyclization of 10a with aqueous sodium hydroxide produced 7-methoxy-3-oxo-1,4-benzoxazine 11a, which upon reduction with lithium aluminum hydride in THF resulted in the formation of 7-methoxy-3,4-dihydro-2H-1,4-benzoxazine 12a. ##STR4##

Sources & evidence

ORD record
ord-ded32ebb34a741c8bdee71d5f9beff47
Source dataset
uspto-grants-1992_06
Patent number
US05118323

Reaction notes

Loading…